title: Saponins esculeosides B-1 and B-2 in Italian canned tomatoes.
abstract: Italian canned tomatoes contain the tomato glycosides esculeosides B-1 (1, 0.0052%) and B-2 (2, 0.0068%) without esculeoside A. Herein, the structure of esculeoside B-1 (1) is characterized to be 3-O-β-lycotetraosyl (5S,22R,23S,25S)-22,26-epimino-16β,23-epoxy-3β,23,27-trihydroxycholestane 27-O-β-D-glucopyranoside. We hypothesized that these substances might be derived from esculeoside A when the cans are prepared with treatment in boiling water. To confirm that hypothesis, we refluxed esculeoside A with water for 6.5 h, providing esculeosides B-1 (1) and B-2 (2) in yields of 25.8% and 31.0%, respectively.
authors.affiliation: Faculty of Pharmaceutical Sciences, Sojo University, Kumamoto 860–0082, Japan.
authors.forename: Hideyuki
authors.initials: H
authors.lastname: Manabe
authors.forename: Yukio
authors.initials: Y
authors.lastname: Fujiwara
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Ikeda
authors.forename: Masateru
authors.initials: M
authors.lastname: Ono
authors.forename: Kotaro
authors.initials: K
authors.lastname: Murakami
authors.forename: Jian-Rong
authors.initials: JR
authors.lastname: Zhou
authors.forename: Kazumi
authors.initials: K
authors.lastname: Yokomizo
authors.forename: Toshihiro
authors.initials: T
authors.lastname: Nohara
mesh_terms: D018551:Solanum lycopersicum / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D012502:Sapogenins / Q000737:chemistry; D012503:Saponins / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D012502:Sapogenins; D012503:Saponins; C530544:esculeoside A; C570315:esculeoside B-1